GB1036521A - Azidoformates and their use in cross-linking polymers - Google Patents

Azidoformates and their use in cross-linking polymers

Info

Publication number
GB1036521A
GB1036521A GB3723/63A GB372363A GB1036521A GB 1036521 A GB1036521 A GB 1036521A GB 3723/63 A GB3723/63 A GB 3723/63A GB 372363 A GB372363 A GB 372363A GB 1036521 A GB1036521 A GB 1036521A
Authority
GB
United Kingdom
Prior art keywords
azidoformate
bis
para
cross
azidoformates
Prior art date
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
Expired
Application number
GB3723/63A
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Hercules Powder Co
Original Assignee
Hercules Powder Co
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Priority claimed from US172815A external-priority patent/US3211752A/en
Application filed by Hercules Powder Co filed Critical Hercules Powder Co
Publication of GB1036521A publication Critical patent/GB1036521A/en
Expired legal-status Critical Current

Links

Classifications

    • D—TEXTILES; PAPER
    • D06—TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
    • D06M—TREATMENT, NOT PROVIDED FOR ELSEWHERE IN CLASS D06, OF FIBRES, THREADS, YARNS, FABRICS, FEATHERS OR FIBROUS GOODS MADE FROM SUCH MATERIALS
    • D06M13/00—Treating fibres, threads, yarns, fabrics or fibrous goods made from such materials, with non-macromolecular organic compounds; Such treatment combined with mechanical treatment
    • D06M13/322—Treating fibres, threads, yarns, fabrics or fibrous goods made from such materials, with non-macromolecular organic compounds; Such treatment combined with mechanical treatment with compounds containing nitrogen
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C247/00—Compounds containing azido groups
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C271/00—Derivatives of carbamic acids, i.e. compounds containing any of the groups, the nitrogen atom not being part of nitro or nitroso groups
    • C07C271/06—Esters of carbamic acids
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08B—POLYSACCHARIDES; DERIVATIVES THEREOF
    • C08B11/00—Preparation of cellulose ethers
    • C08B11/20—Post-etherification treatments of chemical or physical type, e.g. mixed etherification in two steps, including purification
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
    • C08F4/00—Polymerisation catalysts
    • C08F4/04—Azo-compounds
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
    • C08F8/00—Chemical modification by after-treatment
    • C08F8/30—Introducing nitrogen atoms or nitrogen-containing groups
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G63/00—Macromolecular compounds obtained by reactions forming a carboxylic ester link in the main chain of the macromolecule
    • C08G63/91—Polymers modified by chemical after-treatment
    • C08G63/914—Polymers modified by chemical after-treatment derived from polycarboxylic acids and polyhydroxy compounds
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
    • C08K5/00—Use of organic ingredients
    • C08K5/16—Nitrogen-containing compounds
    • C08K5/22—Compounds containing nitrogen bound to another nitrogen atom
    • C08K5/27—Compounds containing a nitrogen atom bound to two other nitrogen atoms, e.g. diazoamino-compounds
    • C08K5/28—Azides
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
    • C08L81/00—Compositions of macromolecular compounds obtained by reactions forming in the main chain of the macromolecule a linkage containing sulfur with or without nitrogen, oxygen or carbon only; Compositions of polysulfones; Compositions of derivatives of such polymers
    • D—TEXTILES; PAPER
    • D06—TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
    • D06M—TREATMENT, NOT PROVIDED FOR ELSEWHERE IN CLASS D06, OF FIBRES, THREADS, YARNS, FABRICS, FEATHERS OR FIBROUS GOODS MADE FROM SUCH MATERIALS
    • D06M13/00—Treating fibres, threads, yarns, fabrics or fibrous goods made from such materials, with non-macromolecular organic compounds; Such treatment combined with mechanical treatment
    • D06M13/10—Treating fibres, threads, yarns, fabrics or fibrous goods made from such materials, with non-macromolecular organic compounds; Such treatment combined with mechanical treatment with compounds containing oxygen
    • D06M13/184—Carboxylic acids; Anhydrides, halides or salts thereof
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C2601/00—Systems containing only non-condensed rings
    • C07C2601/12—Systems containing only non-condensed rings with a six-membered ring
    • C07C2601/14—The ring being saturated

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Health & Medical Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Medicinal Chemistry (AREA)
  • Polymers & Plastics (AREA)
  • Engineering & Computer Science (AREA)
  • Materials Engineering (AREA)
  • Textile Engineering (AREA)
  • General Chemical & Material Sciences (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Biochemistry (AREA)
  • Compositions Of Macromolecular Compounds (AREA)
  • Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)
  • Processes Of Treating Macromolecular Substances (AREA)

Abstract

Para - phenylazophenyl azidoformate (an orange dyestuff) is prepared by reacting para-phenylazophenyl chloroformate with an alkali azide.ALSO:Novel azidoformates having a boiling point of at least 100 DEG C at a pressure of 70 mm. of mercury and having the formula R(O.CON3)x, wherein x is an integer of 1 or more and R is an organic radical inert to cross-linking reactions and containing at least one carbon atom per azidoformate radical, are prepared by reacting a chloroformate of the formula R(O.COCl)x with an alkali azide. Exemplified products are noctadecyl, tetramethylene - bis-, pentamethylene - bis-, 1,4 - cyclohexane - dimethyl - bis-, 2 - (1 - para - menthyl - 8 - yloxy) - ethyl, 2-norborn - 5 - enyl - methylene, a ,a 1 - para -xylylenebis-, phenyl, 2,2 - isopropylidene - bis - para, para1 - phenyl-, 2,21 - oxydiethyl - bis-, 2,21oxydipropyl - bis-, 2,21 - ethylenedioxydiethylbis-, 2,21 - thiodiethyl - bis-, 4,41 - thiodibutylbis-, 3 - hydroxy - 4 - benzoylphenyl and 3,5di - tert. - butyl - 4 - hydroxybenzyl azidoformates, the phosphate ester of para-hydroxyphenyl azidoformate and an azidoformate of the formula C(CH2-O-CH2CH(CH3)-O.CON3)4ALSO:Polymeric materials are cross-linked by heating or irradiating them in the presence of azidoformates having a boiling point of at least 100 DEG C. at a pressure of 70 mm. of mercury and having the formula: (R(O.CON3)x, wherein x is an integer of 1 or more and R is an organic radical inert to cross-linking reactions and containing at least one carbon atom per azidoformate radical. 0.01-20% of the azidoformate may be mechanically mixed with the polymer or added to a polymer solution and heated above its decomposition temperature, e.g. 70-350 DEG C. Exemplified polymeric materials are ethylene-propylene, styrene-butadiene, ethylacrylate-2-chloroethyl vinyl ether, isobutylene-isoprene, butadiene-acrylonitrile and ethylene-propylene-dicyclopentadiene copolymers, polyethylene, cis-1,4-polyisoprene, polyisobutylene, cis-1,4-polybutadiene, polychloroprene, sulphochlorinated polyethylene, polypropylene, polyvinyl chloride, polystyrene, polyethyl acrylate, polyvinyl acetate, poly-(vinyl methyl ether), poly(ethylene oxide), polymeric 3,3-bis-(chloromethyl)oxetane, vinyl modified polydimethyl siloxane, hydroxyethyl cellulose, nitrocellulose, cellulose acetate butyrate, natural rubber, chlorinated natural rubber, polysulphide rubber, polyurethane rubber (based on toluene diisocyanate and a polyalkylene ether glycol) and mixtures thereof. Also included are alkyd resins formed from pentaerythritol, phthalic anhydride and coconut oil, glycerin, phthalic anhydride and soybean oil, glycerin and phthalic anhydride, soybean oil and castor oil, and a reaction product of diallylidene pentaerythritol and triallyl-pentaerythritol. Exemplified cross - linking agents are tetramethylene-bis(azidoformate), 2,21 - oxydiethyl - bis(azidoformate), 2,21-ethylenedioxydiethyl - bis(azidoformate), 2,21-oxydipropyl - bis(azidoformate), 2,21 - thio-diethyl - bis(azidoformate), pentamethylene-bis(azidoformate), n - octadecyl azidoformate, a ,a 1 - xylylene - bis(azidoformate), C(CH2-O -CH2CH(CH3) - O . CON3)4, 2,2 - isopropylidene - bis(para,para1 - phenylazidoformate), 2 - (1 - para - methyl - 8 - yloxy)-ethyl azidoformate, 1,4 - cyclohexanedimethyl-bis(azidoformate) and para - phenylazophenyl azidoformate. The last named compound is also a dyestuff and cross-links to form bright orange rubbery materials. Adhesive and coating compositions are formed by dissolving the above polymers and azidoformates in hydrocarbon, ester or alcoholic solvents which may also contain tetra-, di- and dehydro-abietyl alcohols. Such compositions may be deposited as films. The above cross-linking reactions may also be carried out in the presence of 0.01-1% sulphur and abrasive carbon black fillers, nitrocellulose, toluene, xylene, EtOH, butyl acetate, ethyl acetate, petroleum or polymerized trimethyl dihydroquinoline and phenyl-b -naphthylamine antioxidants.
GB3723/63A 1962-02-12 1963-01-29 Azidoformates and their use in cross-linking polymers Expired GB1036521A (en)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
US172815A US3211752A (en) 1962-02-12 1962-02-12 Cross-linking polymers
US24787862A 1962-12-28 1962-12-28

Publications (1)

Publication Number Publication Date
GB1036521A true GB1036521A (en) 1966-07-20

Family

ID=26868488

Family Applications (1)

Application Number Title Priority Date Filing Date
GB3723/63A Expired GB1036521A (en) 1962-02-12 1963-01-29 Azidoformates and their use in cross-linking polymers

Country Status (7)

Country Link
BE (1) BE628331A (en)
CH (1) CH409995A (en)
DE (1) DE1544993C3 (en)
FR (1) FR1353110A (en)
GB (1) GB1036521A (en)
NL (2) NL143610B (en)
SE (2) SE307669B (en)

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN113234262A (en) * 2021-06-30 2021-08-10 诺博橡胶制品有限公司 High-damping shock-absorbing material for automobile body suspension and preparation method and application thereof

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN113234262A (en) * 2021-06-30 2021-08-10 诺博橡胶制品有限公司 High-damping shock-absorbing material for automobile body suspension and preparation method and application thereof

Also Published As

Publication number Publication date
DE1544993C3 (en) 1975-06-12
NL143610B (en) 1974-10-15
SE307669B (en) 1969-01-13
NL288797A (en)
CH409995A (en) 1966-03-31
DE1544993A1 (en) 1969-09-25
BE628331A (en)
SE335350B (en) 1971-05-24
DE1544993B2 (en) 1974-10-31
FR1353110A (en) 1964-05-29

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